Chebeague Island holiday rentals

We found 762 holiday rentals — enter your dates for availability
Discover a selection of 5 homes and other holiday rentals in Chebeague Island that are perfect for your trip. Holiday homes provide the best amenities for your family, friends or furry companion, such as a fireplace and garden. At the end of the day, you'll find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Chebeague Island

Showing deals for:20 Nov - 27 Nov

2nd Floor: Dining area looks out over the marsh side.
2nd Floor: Spiral stairs lead to ocean view attic bunk room.
2nd Floor: bistro with sliders to the deck and large yard below.
Listen to the waves crash while enjoying the starry night.
Exceptional
(70 reviews)

Spacious Ocean View Getaway, 3 min walk to beach with large fenced in yard

Scarborough

20% off
AU$8,228
for 7 nights, 1 home
AU$1,175 per night
includes taxes & fees
Spacious Ocean View Getaway, 3 min walk to beach with large fenced in yard
Interior
Terrace/patio
Private kitchen
Room
Wonderful
(24 reviews)

Beautiful, single story ranch. Next to city park with ocean view!

Portland

8% off
AU$8,769
for 7 nights, 1 home
AU$1,253 per night
includes taxes & fees
Beautiful, single story ranch. Next to city park with ocean view!
Interior
Interior
Pool
Terrace/patio
Exceptional
(17 reviews)

Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

Scarborough

8% off
AU$5,543
for 7 nights, 1 home
AU$792 per night
includes taxes & fees
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
Exterior detail
Outdoor dining
Interior
The living room leads out to a private deck with a dining table that seats 4.
Exceptional
(42 reviews)

Modern & Sunny House Steps from the Promenade. Private Parking!

Portland

8% off
AU$3,932
for 7 nights, 1 home
AU$562 per night
includes taxes & fees
Modern & Sunny House Steps from the Promenade. Private Parking!
Kitchen
Master Bedroom
Living area
Dining
Exceptional
(34 reviews)

Amazing Oceanfront Brand NewHome Ideal location -

Peaks Island

8% off
AU$7,553
for 7 nights, 1 home
AU$1,079 per night
includes taxes & fees
Amazing Oceanfront Brand NewHome Ideal location -
Kitchen
Casco Bay
picnic area
Dining area
Exceptional
(101 reviews)

Beautiful Oceanfront Apartment, scenic views and water access

Yarmouth

8% off
AU$2,933
for 7 nights, 1 apartment
AU$419 per night
includes taxes & fees
Beautiful Oceanfront Apartment, scenic views and water access
Interior
Interior
Dining
Private kitchen
Exceptional
(31 reviews)

Sunny Spot with Private Parking.

South Portland

8% off
AU$2,235
for 7 nights, 1 apartment
AU$319 per night
includes taxes & fees
Sunny Spot with Private Parking.
Private kitchen
Marina
Dining
Living area
Exceptional
(13 reviews)

Renovated Apartment in Willard Square Area of South Portland, Maine.

South Portland

16% off
AU$2,559
for 7 nights, 1 apartment
AU$366 per night
includes taxes & fees
Renovated Apartment in Willard Square Area of South Portland, Maine.
View from Roof Top deck
Looking up to the house from Garrison Cove
Living Room Fireplace
Kitchen at night with setup for a dinner party
Exceptional
(84 reviews)

Amazing Views, and Comfortable Spaces in this Well Appointed Island Home

Bailey Island

8% off
AU$8,497
for 7 nights, 1 home
AU$1,214 per night
includes taxes & fees
Amazing Views, and Comfortable Spaces in this Well Appointed Island Home
Oven, Keurig, microwave, fridge, toaster, and dishwasher.
Lobby can be accessed from Patton Ct or Exchange St. Door code will be provided.
Everyone's favorite room in the home. Massive 8ftx6ft skylight.
Massive 100 inch smart TV
Exceptional
(6 reviews)

Exchange Street Skylight Loft

Portland

8% off
AU$3,907
for 7 nights, 1 apartment
AU$558 per night
includes taxes & fees
Exchange Street Skylight Loft
Private kitchen
Terrace/patio
View from living room
Living area
Exceptional
(184 reviews)

1 room luxury ocean front studio cottage

Harpswell

8% off
AU$2,177
for 7 nights, 1 apartment
AU$311 per night
includes taxes & fees
1 room luxury ocean front studio cottage
Private kitchen
Living area
Dining
Interior
Exceptional
(133 reviews)

Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants

Portland

12% off
AU$2,950
for 7 nights, 1 apartment
AU$421 per night
includes taxes & fees
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Dining
Outdoor dining
Private kitchen
Living area
Exceptional
(11 reviews)

Peaceful & minutes from the Old Port with private parking

South Portland

8% off
AU$2,208
for 7 nights, 1 apartment
AU$315 per night
includes taxes & fees
Peaceful & minutes from the Old Port with private parking
Living area
Coziest place to relax and unwind have a fire and enjoy the fall and winter
Coffee/ Wine station
Exterior
Exceptional
(67 reviews)

Clean, Cozy, and Professional Waterfront Home- minutes to Portland

Falmouth

8% off
AU$6,303
for 7 nights, 1 home
AU$900 per night
includes taxes & fees
Clean, Cozy, and Professional Waterfront Home- minutes to Portland
Dining
Interior
Exterior detail
Living area
Exceptional
(99 reviews)

2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood

Portland

8% off
AU$2,847
for 7 nights, 1 apartment
AU$407 per night
includes taxes & fees
2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood
Room
Scales in the Old Port for the best seafood
Interior
Discover Victoria Mansion at the bottom of the street.
Exceptional
(53 reviews)

Charming West End Hideaway. Private Parking

Portland

8% off
AU$2,717
for 7 nights, 1 apartment
AU$388 per night
includes taxes & fees
Charming West End Hideaway. Private Parking
View from the top of the Portland Observatory.
Minato is a quick walk away.
Living area
Baharat, across the street from rising tide.
Exceptional
(140 reviews)

Adorable Portland getaway on the Eastern Promenade

Portland

12% off
AU$1,358
for 7 nights, 1 apartment
AU$194 per night
includes taxes & fees
Adorable Portland getaway on the Eastern Promenade
Floors recently refinished.
Property grounds
Kitchen recently renovated.
Open floor plan.
Wonderful
(40 reviews)

Stover's Cove Beach Coastal Retreat

Harpswell

8% off
AU$5,236
for 7 nights, 1 home
AU$748 per night
includes taxes & fees
Stover's Cove Beach Coastal Retreat
Living area
Interior
Walnut topped kitchenette counter with coffee maker.
Room
Exceptional
(43 reviews)

Fresh East End Apartment Walkable to Downtown Portland

Portland

8% off
AU$4,220
for 7 nights, 1 apartment
AU$603 per night
includes taxes & fees
Fresh East End Apartment Walkable to Downtown Portland
Mix of nautical and rustic elements throughout.
5 min car ride to Downtown/Old Port.
Large, well-stocked Kitchen w/stainless steel counter and appliances
Large deck with seating for six, festive lighting and a firepit. Views and sun!
Exceptional
(131 reviews)

City Amenities, Casco Bay Sunrises and Natural Beauty

Portland

6% off
AU$3,103
for 7 nights, 1 apartment
AU$443 per night
includes taxes & fees
City Amenities, Casco Bay Sunrises and Natural Beauty
Room
Interior
Living area
Dining
Exceptional
(20 reviews)

West End's Diamond in the Rough 2-bedroom Apartment with Parking & WiFi

Portland

8% off
AU$4,438
for 7 nights, 1 apartment
AU$634 per night
includes taxes & fees
West End's Diamond in the Rough 2-bedroom Apartment with Parking & WiFi

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    Enjoy full kitchens, laundry, pools, gardens and more

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    More space, more privacy, more amenities — more value

Explore the waterfront setting in Chebeague Island

Enjoy the history and other features of Chebeague Island. Renowned for its shopping, island views and cycling, this city welcomes all visitors. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Sightseeing in and around Chebeague Island

Do you want to find things to do while you're in the area? Venture out of your cosy holiday rental and check out everything that makes Chebeague Island a one-of-a-kind holiday spot. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Happy Wheels Skate Center (11.9 mi / 19.2 km)
  • Brunswick Golf Course (13.6 mi / 22 km)
  • Spring Meadows Golf Course (15.5 mi / 24.9 km)
  • Len Libby Chocolates (16.8 mi / 27.1 km)
  • Ash Cove Pottery (4.8 mi / 7.7 km)
  • Land's End Gift Shop (5.5 mi / 8.9 km)

Exploring the natural features in Chebeague Island

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Chebeague Island is a great place to spend some time outside. Here are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Winslow Memorial Park (4.3 mi / 6.9 km)
  • Casco Bay (6.5 mi / 10.4 km)
  • Sand Beach (7.5 mi / 12 km)
  • East End Beach (8.3 mi / 13.4 km)
  • Eastern Promenade (8.4 mi / 13.5 km)
  • Desert of Maine (8.5 mi / 13.7 km)

Transport options to and around Chebeague Island

The nearest airport is in Portland, ME (PWM-Portland Intl. Jetport), located 12.1 mi (19.4 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Auburn, ME (LEW-Auburn - Lewiston Municipal), which is 23 mi (37.1 km) away.

Frequently asked questions

Where are the best areas for renting a beach house in Chebeague Island?
For renting a beach house in Chebeague Island, visitors should explore the charming areas near the island's coastline, particularly around the Chebeague Island Marina and the local beaches like the historic Chebeague Island Inn. Here, you can find a variety of beach houses that provide convenient access to sandy shores and beautiful views of Casco Bay. Many properties in this area come equipped with modern amenities such as outdoor decks for enjoying sunny afternoons, fully stocked kitchens for self-catering, and living spaces designed for relaxation after a day of beach activities.In addition, the vicinity to the Chebeague Island Library and local shops adds a quaint charm, making it easy for guests to enjoy local culture and conveniences. Some homes may also feature private docks, allowing for easy access to boating and fishing activities. The island's natural beauty is complemented by scenic walking trails that meander through lush landscapes, providing opportunities for outdoor exploration.
What is the most popular type of holiday rental accomodation in Chebeague Island?
In Chebeague Island, holiday houses and cottages are the most popular types of holiday rentals, with several available throughout the island. These properties typically offer a charming and comfortable atmosphere, ideal for a relaxing getaway. Most rentals feature fully equipped kitchens, spacious living areas, and outdoor spaces such as decks or patios, allowing guests to enjoy the picturesque surroundings. The island's serene environment makes these accommodations superb for families or groups looking to unwind while exploring local attractions like the Chebeague Island Historical Society and the beautiful beaches.
Are there any family house rentals in Chebeague Island?
In Chebeague Island, Maine, there are several family-friendly house rentals available, making it an excellent choice for those seeking a memorable getaway. The island is known for its tranquil atmosphere and stunning coastal views, superb for families looking to unwind.Many homes feature spacious layouts with multiple bedrooms, ideal for accommodating larger groups. Visitors can expect amenities such as fully equipped kitchens, allowing for family meals, and inviting living areas where everyone can gather. Some properties even offer outdoor decks or patios, where children can play and adults can enjoy the fresh sea air.The island is also in close proximity to beautiful beaches, making it easy for families to spend their days swimming, building sandcastles, or exploring the shoreline. Additionally, local parks provide opportunities for outdoor activities, such as hiking and picnicking.
Can I rent a holiday home with a pool or hot tub in Chebeague Island?
In Chebeague Island, there are several holiday homes available for rent that feature pools or hot tubs. This picturesque island in Maine offers a serene escape with its stunning coastal views and charming surroundings. Many properties boast private pools or hot tubs, superb for relaxation after a day of exploring the island.Travellers can expect amenities such as spacious outdoor areas, fully equipped kitchens, and comfortable living spaces, making these rentals ideal for families or groups looking to enjoy a tranquil getaway.
Are there pet-friendly house rentals in Chebeague Island?
In Chebeague Island, visitors will find several pet-friendly house rentals that cater to both comfort and convenience. Many of these properties offer amenities such as fully equipped kitchens, outdoor spaces, and comfortable living areas, making them ideal for families or groups travelling with pets.The island is surrounded by stunning natural beauty, with easy access to walking trails and beautiful waterfront areas where pets can enjoy the outdoors. Chebeague Island itself is known for its charming coastal scenery, offering opportunities for leisurely strolls along the beach or exploring local parks.Additionally, the community atmosphere on the island is welcoming, with local shops and eateries that often embrace pet-friendly policies, allowing you to enjoy a meal or a coffee with your furry companion nearby.
Are there any remote work holiday rentals in Chebeague Island?
In Chebeague Island, there are several holiday rentals suitable for remote work. The island's tranquil environment, combined with its picturesque views of the water, makes it an appealing choice for those looking to balance work and leisure. Many of the properties offer amenities such as Wi-Fi in rooms and access to third-party internet services, ensuring that you can stay connected while enjoying the serene surroundings.The charming island also features opportunities for outdoor activities, with scenic walking trails and beautiful coastlines nearby. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Chebeague Island?
In Chebeague Island, popular holiday rental amenities include outdoor spaces like decks and patios, allowing guests to enjoy the scenic surroundings. Most rentals come equipped with kitchens, enabling travellers to prepare their own meals. Many properties also feature porches or lanais, great for relaxing while taking in the coastal views. Families will appreciate the availability of children's books in some accommodations, adding a thoughtful touch for young guests.
When is the best time to visit Chebeague Island for a holiday rental?
The best time to visit Chebeague Island for a holiday rental is during the summer months, particularly in July, when the island is at its vibrant peak. This season, which spans from June to August, draws many visitors eager to bask in the sun and partake in the various outdoor activities that the island offers. With warm temperatures averaging around 20 to 25 degrees Celsius, it's an ideal time for swimming, kayaking, and leisurely strolls along the sandy shores.In July, the atmosphere is lively, with both locals and tourists enjoying the island's charm and hospitality. You'll find plenty of opportunities to explore the picturesque landscapes, indulge in fresh seafood, and experience the local culture through various summer events and festivals. The scenic beauty of Chebeague Island, coupled with its numerous family-friendly activities, makes it a superb holiday destination during this time.For those looking for a more budget-friendly option, consider visiting in November. This month offers a quieter experience, allowing you to enjoy the natural beauty of the island without the summer crowds. You can take peaceful walks along the beaches and appreciate the stunning coastal views at a leisurely pace.Ultimately, your ideal time to visit Chebeague Island will depend on whether you prefer the bustling energy of summer or the tranquil beauty of the off-peak season.
What are the top attractions in Chebeague Island?
Chebeague Island is a charming destination known for its natural beauty and relaxed atmosphere. Visitors can explore the island's stunning beaches, such as the sandy shores of Chandler's Cove, superb for sunbathing and picnicking. The island's scenic walking trails, particularly around the Chebeague Island Historical Society, offer insights into local history and stunning views of Casco Bay.The Chebeague Island Yacht Club is a focal point for water sports enthusiasts, providing opportunities for sailing and kayaking. The local community also hosts events and markets, giving visitors a taste of island life and the chance to interact with residents.
Are all fees included in the Chebeague Island holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Chebeague Island holiday homes with parking?
Stayz offers a wide selection of holiday homes in Chebeague Island with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Chebeague Island holiday homes?
You can find great discounts on holiday homes in Chebeague Island on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Chebeague Island holiday home booking on Stayz?
To find Chebeague Island holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Chebeague Island?
A long-stay holiday home in Chebeague Island is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Chebeague Island holiday home?
Book your Chebeague Island holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Chebeague Island?
Prices for holiday homes in Chebeague Island vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Chebeague Island to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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